tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

HRID 718627Notes

Reaction equation

HRID 718627 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=1>CO.[Pd]>[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[CH:18]1[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]1

Participants

4

Reactant 1

HCID 117733826tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 117733827tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 41a (3.5 g, 8.4 mmol) in methanol (30 mL) was added 10% Pd/C (ca. 50% water, 3.5 g). The resulting mixture was hydrogenated at about 2 to 3 atm overnight, and filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure to obtain compound 41b as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H31N5O4: 418.2 (M+H). found: 418.2.

Workup

  1. customwas hydrogenated at about 2 to 3 atm overnight
  2. filtrationfiltered through a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0ebba9e8fb21485bb6d5065c452ad4f7
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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